Dimethylformamide → HCID 86618258, compound

HRID 1159821Notes

Reaction equation

HRID 1159821 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:12][N:13]([CH3:15])[CH3:14])=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[H-].[Na+].[F:18][C:19]([F:31])([F:30])[C:20]1[CH:21]=[C:22]([S:26](Cl)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1.CN([CH:35]=[O:36])C>O>[F:18][C:19]([F:31])([F:30])[C:35]([OH:36])=[O:2].[CH3:1][O:2][C:3]1[C:4]([CH2:12][N:13]([CH3:14])[CH3:15])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:19]([F:18])([F:30])[F:31])[CH:21]=1)(=[O:28])=[O:27])[CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Product 1

HCID 86618258HCID 86618258, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine (23.5 mg, 0.115 mmol; Intermediate 79) was distributed in two portions in DMF, NaH (60%) added and the mixture was stirred for 30 min before adding 3-trifluoromethylbenzene-sulfonyl chloride (56.3 mg, 0.230 mmol). The reaction mixture was diluted with water and extracted with DCM, dried and concentrated. This residue was purified by preparative HPLC. Yield: 7 mg. MS (ESI+) for C19H19F3N2O3S m/z 413 (M+H)+.

Workup

  1. extractionextracted with DCM
  2. customdried
  3. concentrationconcentrated
  4. customThis residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-4e799441fc374398b1ad738f76b042f1
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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